Search B&B in Pittsfield

    Plan, book, stay with confidence
    bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Compare 27 B&B in Pittsfield with updated reviews, rates, and availability.

The Cornell Inn, Lenox
3.0 star property
8.6 out of 10, Excellent, (1000)
"Property was so cute! Only a 10 minute walk to downtown and the breakfast offered was delicious. Would recommend to friends who want to explore the Berkshires! "
The price is SAR 458
SAR 532 total
includes taxes & fees
9 Jum. II - 10 Jum. II
The Cornell Inn, Lenox
Lakehouse Inn
4.0 star property
9.6 out of 10, Exceptional, (155)
"They greeted us as soon as we checked in with apple cider and brownies. The room was super cute. Breakfast was delicious. The only negative was it could be noisy when people are walking in hallway. We will definitely stay again. "
The price is SAR 495
SAR 575 total
includes taxes & fees
3 Jum. II - 4 Jum. II
Lakehouse Inn
Brook Farm Inn
3.5 star property
9.4 out of 10, Exceptional, (136)
"This is a charming and very pleasant place to stay."
The price is SAR 754
SAR 842 total
includes taxes & fees
3 Jum. II - 4 Jum. II
Brook Farm Inn
Save an average of 15% on thousands of hotels when you're signed in
Shaker Mill Inn
2.5 star property
9.6 out of 10, Exceptional, (385)
"Quaint "
The price is SAR 847
SAR 929 total
includes taxes & fees
3 Jum. II - 4 Jum. II
Shaker Mill Inn
Inn at Silver Maple Farm
3.0 star property
9.8 out of 10, Exceptional, (68)
"This place was absolutely magical!! The customer service here is just off the charts. Breakfast was amazing. Views were great. Definitely recommend "
The price is SAR 634
SAR 685 total
includes taxes & fees
3 Jum. II - 4 Jum. II
Inn at Silver Maple Farm
Whistler's Inn Bed & Breakfast
3.5 star property
7.6 out of 10, Good, (433)
"Gorgeous loved large home where you will feel at home. Lots of antiques, books. Grand piano. Hosts very welcoming. No air conditioning. Hot showers once hot water heater turned on. First night unfortunately cool shower. Dog friendly. Breakfast choice fine. So near to Lennox (easy walk downhill) and close to Tanglewood. Really comfortable beds. This is an old house built in 1867 and there are many ongoing minor repairs to do with walls. Highly recommend and looking forward to returning. "
The price is SAR 516
SAR 577 total
includes taxes & fees
2 Jum. II - 3 Jum. II
Whistler's Inn Bed & Breakfast
Chambery Inn
3.0 star property
9.6 out of 10, Exceptional, (356)
"Amazing place.."
The price is SAR 934
SAR 1,043 total
includes taxes & fees
2 Jum. II - 3 Jum. II
Chambery Inn
33 Main
4.0 star property
10.0 out of 10, Exceptional, (63)
"I love the fact that it only had eight rooms they had happy hour from 5 to 6 PM so we are able to meet other people at the hotel. I love the rooms and the cleanliness and especially the breakfast they were amazing and delicious!! I would recommend this hotel highly!"
The price is SAR 1,452
SAR 1,621 total
includes taxes & fees
2 Jum. II - 3 Jum. II
33 Main
The Barrington
4.0 star property
9.6 out of 10, Exceptional, (99)
"As always, our stay at The Barrington was wonderful. The rooms are large, lovely and the bed comfortable. The service is great and everyone is so friendly and accommodating! The breakfast is delicious. We truly enjoy our stay, every time!"
The price is SAR 1,219
SAR 1,362 total
includes taxes & fees
2 Jum. II - 3 Jum. II
The Barrington
Granville House
3.0 star property
10.0 out of 10, Exceptional, (70)
"Very nice hosts and lovely and inventive decor."
The price is SAR 1,031
SAR 1,152 total
includes taxes & fees
2 Jum. II - 3 Jum. II
Granville House
The Inn at Stockbridge
4.0 star property
9.6 out of 10, Exceptional, (94)
"Fantastic!"
The Inn at Stockbridge
The Trail in Adams - Berkshires’ Art Hotel
2.5 star property
8.8 out of 10, Excellent, (104)
"It was clean and quiet good Breakfast "
The price is SAR 820
SAR 916 total
includes taxes & fees
2 Jum. II - 3 Jum. II
The Trail in Adams - Berkshires’ Art Hotel
Devonfield Inn B&B
4.0 star property
10.0 out of 10, Exceptional, (106)
"The classic character of the Inn is so beautiful and adds to the whole experience!"
The price is SAR 1,272
SAR 1,420 total
includes taxes & fees
12 Jum. II - 13 Jum. II
Devonfield Inn B&B
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
4.5 star property
9.2 out of 10, Wonderful, (101)
"The b&b was so beautiful and unique! The area was serene. The host was very sweet and accommodating."
The price is SAR 1,721
SAR 2,082 total
includes taxes & fees
3 Jum. II - 4 Jum. II
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Inn at Kenmore Hall
3.0 star property
10.0 out of 10, Exceptional, (25)
"Gorgeous grounds, welcoming home atmosphere. wonderful breakfast and staff that made it feel like home - only better! "
Inn at Kenmore Hall
Tanglewood Suites
2.5 star property
8.0 out of 10, Very Good, (15)
"The property is so lovely and peaceful. I love the classic mid-century modern aesthetic. For visitors to the National Shrine of Divine Mercy, the Inn’s location couldn’t be more perfect with only a 5-minute walk to the Shrine. "
Tanglewood Suites
Romantic Boutique Hotel / Bed and Breakfast - Standard Queen Handicap Accessible
9.8 out of 10, Exceptional, (10)
"We would return to the inn again. Bob was wonderful and very, very accommodating:-)"
The price is SAR 3,747
SAR 4,780 total
includes taxes & fees
2 Jum. II - 3 Jum. II
Romantic Boutique Hotel / Bed and Breakfast - Standard Queen Handicap Accessible
Romantic Boutique Hotel / Bed and Breakfast - Smallest Room in The Berkshires
2.0 out of 10, (1)
"Never even met the inn keepers...no one is in sight...WiFi wouldn’t work...a/c in room would not stay on.....1 item only for breakfast- delivered to room- that has no table or chair- stood in the bathroom to eat!!!! Very expensive for what u get "
The price is SAR 1,121
SAR 1,424 total
includes taxes & fees
16 Jum. II - 17 Jum. II
Romantic Boutique Hotel / Bed and Breakfast - Smallest Room in The Berkshires
Harbour House Inn
3.5 star property
9.4 out of 10, Exceptional, (48)
"Decorations were beautiful, room and bed were so comfortable, hostess and food were wonderful. Brandi was thoughtful in every way possible. Can't go wrong choosing this place over a chain. Love it!"
The price is SAR 927
SAR 980 total
includes taxes & fees
3 Jum. II - 4 Jum. II
Harbour House Inn
Romantic Boutique Hotel / B&B - Deluxe Firespa Suite
10.0 out of 10, Exceptional, (4)
"The property was a converted parochial school The rooms were old class rooms. Very spacious and extremely comfortable. Lots to do in the area or like we did just relax . We would recommend the inn for a great summer getaway . Community theater is a big attraction although not open yet Enjoy"
The price is SAR 3,751
SAR 4,785 total
includes taxes & fees
2 Jum. II - 3 Jum. II
Romantic Boutique Hotel / B&B - Deluxe Firespa Suite
Don't see what you're looking for?
See all available properties in Pittsfield
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Other property types in Pittsfield

Chic Pittsfield Home With A View!
9.0 out of 10, Wonderful, (4)
"Nicely decorated and clean. It had everything we needed, including kitchen supplies and detergent for the washer/dryer. Great rental for our family getaway."
Chic Pittsfield Home With A View!
Jiminy Peak Mountain Resort
3.0 star property
8.2 out of 10, Very Good, (858)
"Staff were so attentive, even at the late hour we checked in (10pm) the place had everything you need. Amazing views and amenities. Loved it"
The price is SAR 596
SAR 654 total
includes taxes & fees
2 Jum. II - 3 Jum. II
Jiminy Peak Mountain Resort
Cabin w/3 Acres, Tennis+BBall Courts by 4 Ski Mtns
9.8 out of 10, Exceptional, (32)
"We loved our time, very cozy cabin"
Cabin w/3 Acres, Tennis+BBall Courts by 4 Ski Mtns
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Frequently asked questions

Searching for B&Bs in Pittsfield?
If you’re looking for something a little more offbeat than your standard hotel, a stay at a bed and breakfast might be the perfect option for your vacation. While you’re here, you can get to know Pittsfield by exploring its natural beauty. Consider a stop by Pittsfield State Forest and Canoe Meadows Wildlife Sanctuary.
How do you know if a B&B is the right choice for your stay?
With attentive service, opportunities to meet guests from other places, and delectable breakfasts, B&Bs provide a unique setting.
When should I stay at a B&B in Pittsfield?
When you’re dreaming of a getaway to Pittsfield, year-round temperatures and rainfall may be important factors to consider. The hottest months are usually July and August with an average temp of 66°F, while the coldest months are January and February with an average of 27°F. The snowiest months in Pittsfield are January, March, February, and November, with each month seeing an average of 7 inches of snowfall.
What is there to do in Pittsfield?
When you want to explore some cultural attractions on your trip, Berkshire Museum and Colonial Theater are worthy sites to check out. You might put Barrington Stage Company and Bousquet Ski Area on your list if you want to see more of the area.
How can I get to and around Pittsfield?
Planning your excursions in and around Pittsfield is easier with these transportation options. Fly into Pittsfield, MA (PSF-Pittsfield Municipal), which is located 2.5 mi (4 km) from the city center. You can also search for flights into Hudson, NY (HCC-Columbia County), which is 25.7 mi (41.4 km) away. If you’d like to venture out around the area, you may want a rental car for your journey.

Recent reviews of Pittsfield hotels
Expedia verified reviews